Pegging and It's Perks
I was interning at a now-defunct erotic magazine when I met our resident dominatrix at the office Christmas party. She asked me if I wanted to be her vanilla girl assistant, and as I wasn’t getting paid there, I thought, I might as well try.
Back then, I knew nothing about pegging—I hadn’t even seen it in porn. We called it strap-on play back then [the term pegging was coined by sex columnist Dan Savage in 2001]. She had to teach me everything. She showed me her equipment: the leather harness that was specially made, her various cocks of different colors, widths, and shapes.
I watched her do it to other people and saw the pleasure that men got out of it—there are huge swathes of men in the world who are desperate to be pegged. The sight of a beautiful woman dressed up in black leather gear wearing a harness and a cock is magnificent! It’s triumphant. Everyone should see it at some point in their life.
One time, a guy requested a strap-on session with the dominatrix. His dream was to be penetrated by two women separately. It started with a spanking session and some small penis humiliation, and then the dominatrix made him worship her cock. After a while, she was like, "Enough of this, it’s time to get fucked."
She spread him on all fours, propping him on his forearms. Then she put a condom over her cock, got tons of lube, and started off using her fingers to get him loose enough. She slid into him, thrusting quite gently at first and then building up the pace and depth; he wanked himself off at the same time.
He came, and then after he’d rested for a bit, she said, "Jamie"—that was my fake name back then—"is going to lose her strap-on virginity."
We’d bought my cock and harness the week before; It was a good six inches long and a nice girth. I remember being pleased with the overall effect when I looked in the mirror. The dominatrix put a condom on me, lubed me up, and showed me what to do. He was already open by that point, so I didn’t have to break him in again—I just entered him. I remember it so distinctly; it was mesmerizing.
Pegging him changed my perspective on sexuality. I became more empathetic to men. Fucking someone is, physically, quite hard work. When I was younger I didn’t put that much effort in when I was having sex, in terms of thrusting or doing the actual maneuvering. Also, when someone is opening their body to you, they’re quite vulnerable—you have a magnificent amount of power. I’d never thought about sex like that before because I’d never felt physically vulnerable in that way.
I carried on working as a dominatrix, seeing my own clients. Often, you’d find yourself having to disappoint clients who’d seen hardcore porn where people are being absolutely rammed, and they’d want it really full on. But if you haven’t done it much, you can’t take it like that. When you start to feel the resistance in someone’s body, you have to stop; otherwise you’re going to hurt them. So the fantasy doesn’t always match up to the reality.
It’s hard for me to peg someone I’m in love with. There’s an exchange of energy—for nearly all men, there will be some unsettling feelings afterwards. Even if they fantasize about submitting to women, there’s this fear that you’ve given up something in the process of letting women fuck you. Men can feel belittled, upset, or regretful afterwards—which is interesting, because women allow men to fuck them all the time, but they don't feel subjugated.
After I'd finished working as a dominatrix, I was quite cagey about pegging men in romantic relationships. Even if guys said they liked it, I felt like they were seeing the dom, not the person. I did meet a romantic partner who was really into pegging, and I felt proud of him for being really honest about his desires.
We pegged a couple of times a year. I remember the first time we did it he was lying on his back looking up at me, so we could kiss at the same time. It was more intimate—less about getting rammed, and more about him relinquishing to me. For a man to give that up is quite sexy.
We probably pegged for about 15 minutes. It was a very wholesome sexual experience; we were both very engaged and present. It was sensual and loving, not about humiliation. That’s what’s great about pegging. It can be whatever you want it to be—the limit is your imagination.
A strap-on has to feel like an extension of your body in order for you to be really in control of it. It’s best to buy a harness, and separate differently-sized cocks, as they tend to be better quality and you can work your partner up through the different sizes.
Lots of men are apprehensive about being dirty, which prevents them from being able to let go and enjoy it. If you’ve got someone who’s pegging-curious, get them in the shower and soap them up to help them relax. Don’t give them an enema—that can leave water in the body, creating more chaos. You’ll need lots of lube.
Everyone is capable of pegging. You have to build up to it gradually and find the right man who’s genuinely interested in it. I think a surprising number of men are into it and want to try it. And lots of women would gain sexual confidence from pegging.
Once I felt like I could wield a cock and dominate someone in that way, things flipped for me. Pegging men helped me not to be as afraid of male sexuality. I saw how vulnerable men can be— if they are open enough.